Methanol → 2-Methoxy-3-(4-tetradecylphenoxy)-1-propanol

HRID 235724Notes

Reaction equation

HRID 235724 reaction equation
[CH3:1][O:2][CH:3]([CH2:26][O:27]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:8][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>O1CCCC1>[CH3:1][O:2][CH:3]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:10][CH:11]=1)[CH2:26][OH:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 202185881-[2-Methoxy-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene

Product 1

HCID 202189912-Methoxy-3-(4-tetradecylphenoxy)-1-propanolYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of about 527 mg of 1-[2-methoxy-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene, about 10 mg of p-toluenesulfonic acid and about 5 ml of methanol:tetrahydrofuran (about 1:1) was stirred under argon for about 16 hours and the solvents removed under reduced pressure. The residue was dissolved in ether:hexane (about 1:1), washed with aqueous sodium bicarbonate, brine, dried and evaporated, giving about 171 mg of the desired title compound, mp 43°-45° C.

Workup

  1. customthe solvents removed under reduced pressure
  2. dissolutionThe residue was dissolved in ether
  3. washhexane (about 1:1), washed with aqueous sodium bicarbonate, brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-762352ae57a042cb825608bf5a7c4b4e
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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